Hydroxy-[2-[methyl(5-phenylpentyl)sulfonio]-1-phosphonoethyl]phosphinate | 960593-08-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: Hydroxy-[2-[methyl(5-phenylpentyl)sulfonio]-1-phosphonoethyl]phosphinate
• CAS: 960593-08-2
• 化学式: C₁₄H₂₄O₆P₂S
• 分子量: 382.354
• InChiKey: MZTRXKTVKIJPJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-Methylsulfanylpentylbenzene 、 vinylidene-1,1-diphosphonic acid 在 三氟乙酸 作用下， 以58%的产率得到Hydroxy-[2-[methyl(5-phenylpentyl)sulfonio]-1-phosphonoethyl]phosphinate
  参考文献：
  名称：

  Activity of Sulfonium Bisphosphonates on Tumor Cell Lines

  摘要：

  We investigated three series of sulfonium bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines. The first series consisted of 6 cyclic sulfonium bisphosphonates, the most active species having an (average) IC50 of 89,mu M. The second consisted of 10 phenylalkyl and phenylalkoxy bisphosphonates, the most active species having an IC50 of 18,mu M. The third series consisted of 17 n-alkyl sulfonium bisphosphonates, the most active species having an IC50 of similar to 240 nM. Three QSAR models showed that the experimental cell growth inhibition results could be well predicted. We also determined the structures of one sulfonium bisphosphonate bound to farnesyl diphosphate synthase, finding that it binds exclusively to the dimethylallyl diphosphate binding site. These results are of interest since they show that sulfonium bisphosphonates can have potent activity against a variety of tumor cell lines, the most active species having IC50 values much lower than conventional nitrogen-containing bisphosphonates.

  DOI：

  10.1021/jm700991k

文献信息

• Activity of Sulfonium Bisphosphonates on Tumor Cell Lines
  作者：Yonghui Zhang、Michael P. Hudock、Kilannin Krysiak、Rong Cao、Kyle Bergan、Fenglin Yin、Annette Leon、Eric Oldfield

  DOI：10.1021/jm700991k

  日期：2007.11.1

  We investigated three series of sulfonium bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines. The first series consisted of 6 cyclic sulfonium bisphosphonates, the most active species having an (average) IC50 of 89,mu M. The second consisted of 10 phenylalkyl and phenylalkoxy bisphosphonates, the most active species having an IC50 of 18,mu M. The third series consisted of 17 n-alkyl sulfonium bisphosphonates, the most active species having an IC50 of similar to 240 nM. Three QSAR models showed that the experimental cell growth inhibition results could be well predicted. We also determined the structures of one sulfonium bisphosphonate bound to farnesyl diphosphate synthase, finding that it binds exclusively to the dimethylallyl diphosphate binding site. These results are of interest since they show that sulfonium bisphosphonates can have potent activity against a variety of tumor cell lines, the most active species having IC50 values much lower than conventional nitrogen-containing bisphosphonates.